Haglund’s syndrome (HS) is a painful condition that is caused by an exostosis of the posterior superior part of the calcaneus coupled with Achilles tendinopathy and retrocalcaneal bursitis. Both for the proper musculoskeletal assessment and for the differential diagnosis process of possible concurrent diseases deriving from other anatomical areas, the diagnosis of HS is still a challenge. Case Presentation: A 41-year-old male amateur runner was diagnosed and treated for low back pain and referred leg pain by his general practitioner. Due to ineffective results, he self-presented to a physical therapist (PT) with intense right heel pain, radiating up to the leg and to the lumbopelvic region. Results: The PT’s examination and interview relating to the sports activities led to the correct diagnosis and a proper orthopedic referral. At the one-year follow-up, the patient reported regular pain-free marathon running. Discussion: This case report highlights the central role of PTs working in direct access environments as primary care healthcare professionals for the management of musculoskeletal diseases, and their abilities in identifying patients with suspected pathologic conditions that may need referral for imaging, medical assessment or surgical intervention.